My clothes are boring.

July 2, 2008 6:56 PM

I'd like to punch up my wardrobe a little, but I don't know what to do. Advise me!

Like many hackers, I can't dress for shit. My everyday outfit is a pair of corduroys, a tee shirt (often with slogans ranging from smarmy to offensive; a relic of my punk rock sympathies), and a pair of hiking shoes or sneakers. Sometimes a button-up shirt, untucked. Almost exclusively solid colors—lots of earth tones, and lots of gray. I wear the same things week in and week out.

It's comfortable, and I'm fine with that if I'm just hanging out at home, crawling around the server room, or picking up some groceries. But sometimes I want a little more color (not necessarily literal) and personality to my look.

Here's the problem: I can't find anything—anything—that feels like me. The men's fashion at mainstream clothing stores is either dad-in-a-minivan conservative, or just plain ridiculous—sometimes I have to double-check to make sure I haven't wandered into the "Young Men's" section. Commercial fashion in general all seems to be designed to brand you as a member of one tribe or another, or to prove how much money you have, and I want none of that. For that matter, I don't really belong to any tribes, so I'm not sure whose uniform I'd wear, anyway. And the only way you'll ever see me in a pair of khakis is if you kill me and put me in them.

I've had some luck at vintage clothing stores, but the pickings are slim; the ones around here cater mainly to women. I also wonder if losing my spare tire would make me more comfortable in slightly showier styles. Yeah, it probably would.

I'm 31 and male (if you hadn't figured that out yet). I'm smart and scientifically minded. I'm pretty introverted (so bright colors and busy patterns would probably not be very "me"). My hair is blond, and I wear it pretty short; I don't have a beard, but I often sport a day or two of stubble (I'm getting better about keeping up with that).

I like hiking and the outdoors ("vaguely outdoorsy hacker-casual" is a decent description of my current wardrobe), but I'm not hardcore enough to be one of those people who wears outdoor stuff all the time. I'm politically independent (ex-anarchist), with no particular allegiance to the Left but bristling antipathy toward the Right. I like my music psychedelic, electronic, and/or art-damaged. I'd like to maintain at least a token of countercultural sentiment, because that's part of who I am—but, at the same time, I want to look like a mature guy who knows shit about wine and calls a few of the shots at work, because that's also part of who I am. So, y'know, classy and grown-up, but at the same time bohemian-intellectual. Or something.

I don't mind spending money on the right stuff. And I don't want to look like I'm trying too hard. :)

I realize this is hopelessly vague. Any suggestions are appreciated!

posted by greenie2600 to Clothing, Beauty, & Fashion (24 answers total)

For your hopelessly vague details, a perhaps hopelessly vague suggestion: if you don't already, get clothes that fit better. You don't even necessarily have to change up the style. To illustrate, take the fairly standard t-shirt/jeans/sneakers look. Three basic items that can either make you look like a handyman, a geek, or ready for a casual night out. One thing that the hacker look seems to rely on is baggy clothes; wear slimmer shirts and jeans, while keeping in mind your body style (i.e. don't wear too-tight shirts while you've got that spare tire). Also, the trend these days is to err on the side of jeans with legs that are too long, as opposed to jeans that are too short (and show off your white socks—which, by the way, you may want to drop). Finally, specific styles seem to call for bulky sneakers, but you're probably better off with either a pair of Chucks or else more "urban" sneakers—not in the hip-hop sense, but in the not-for-athletics sense.

As I'm not so stylish myself, I'll leave others to give you more advanced advice, but that's what's worked for me.
posted by chrominance at 7:09 PM on July 2, 2008

Is there anyone (male or female) who's style you like that you could point us to? If not start looking out for people like that and take note of what you do and don't like about the way they dress.
posted by Airhen at 7:09 PM on July 2, 2008

Ben Sherman menswear has a long history of smart-casual countercultural cred... I think lots of their pieces could work for plenty of guys in achieving a kind of smart-casual urban look (ignore the emo hair and white belts on some of the models).
posted by scody at 7:17 PM on July 2, 2008 [1 favorite]

You don't want to look like you're trying too hard? Then you're already halfway there.


This is a no-brainer:

Ralph Lauren and to a lesser degree, J Crew. Low key, well-made, good-looking everyday clothes that are not fashion (they're a style). The classics are never boring. That's why they are classic.

Once you have adopted this style, all of your worries about clothing and whether or not you look good will vanish - for good.
posted by Zambrano at 7:22 PM on July 2, 2008 [1 favorite]

This isn't a slam, but for someone who doesn't want to be defined by their clothes, you sure put a lot of definitions on them. Sure, there are "uniforms" out there, but in general, you are NOT what you wear.

Why don't you hit a few stores and just try on some clothes? See what looks good on you. Turn off the "I'm an ex-anarchist, hacker, punk dude" filter and just look at yourself. Once you decide what colors, styles, cuts look good in an objective way, you can spend a little time refining your look subjectively. You're stuck in a fashion rut - but you're going to have to get out your mental one in order to have any hope of updating your look.
posted by The Light Fantastic at 7:30 PM on July 2, 2008

I don't want to look like I'm trying too hard.

I think you might be, though.
posted by box at 7:38 PM on July 2, 2008

A warning about ben sherman - see if you can find a place to try this stuff on - Ben Sherman shirts, at least, run small (meaning cut for thin dudes) and are not designed for men with spare tires - I think they have one fit that is a little more accommodating, but most of their stuff (the 'Carnaby', I think, is their most common cut for shirts) runs thin. This from an ex-spare tire dude.

What about places like Nordstrom Rack or Banana Republic (if available)?

You also might try better jeans - if you have a 'jeans bar' type store nearby that sells a large variety of designer jeans you should be able to find somebody there to help you find a brand that fits you well. It might seem absurd to drop a hundred bucks or more on jeans, but having high quality pants that fit can go a long way to improving your style.
posted by drobot at 8:04 PM on July 2, 2008

I feel for you. I, too, go to the store and ask myself who would want to wear this crap. Not only that, almost nothing feels like it fits right. Too tall, wide ass ('cause of my biking?) but still a bit on the heavy side (not biking enough!).

Dockers usually work for me, and loose polo shirts, and lightweight sweaters. A pair of dark dress slacks actually worked quite fine, the best fit I found EVER, until they got one hole too many - thrashing in them one time too many, I guess. Now, um, no can find that style/fit in the stores.... Serious frowny face :(

I'm kind of a goth-by-artistic & philosophic-temperament, so I tend to the dark colors, or a black t-shirt under a collared work shirt. It can look neat, appropriate for the office, but also gets my inner angst out.

You can probably do the same with a post-punk attitude. It's not "you are what you wear" but, "wear what you are," eh? Good luck.
posted by madmatx at 8:05 PM on July 2, 2008

Next time you're at a mall, ballgame, bar, city park, office meeting, take note of what you see folks wearing that you think looks good on them. Do a little analysis of Why ?
If you have a woman significant in your life , ask for suggestions , take a trip with S.O. to the thrift store and blow some bucks on what ever catches your eye. Wear it, if it sucks, re-donate. Experiment.
posted by Agamenticus at 8:07 PM on July 2, 2008

Response by poster: Thanks for the replies so far.

chrominance, I've already got most of your advice down, but I do wear white socks. Other people have mentioned this to me, actually.

TLF, you're right, of course. I have just gone to stores and tried things on—many times. And none of it feels right.

Airhen: these guys are pretty much my heroes, but other than that, I can't think of anyone. It's a good question...I'll keep it in mind.

scody: that's kinda what I'm after. Maybe a little less indie-rock/fashion-designery, though. I'll poke through their catalog and see what I can find.

I think you might be, though.

I can see why you'd say that. It's just that I honestly don't understand this "fashion" thing, and on some level I actually distrust it as superficial and pretentious. So no matter what I try on, I feel like I'm doing something forced and unnatural. At the same time, I do want to look nicer. I just don't want to feel forced and unnatural while doing it. Therein lies the conundrum.
posted by greenie2600 at 8:11 PM on July 2, 2008

Vest and hat, vest or hat.
posted by Civil_Disobedient at 8:25 PM on July 2, 2008

J Crew is really not bad IMHO. The chinos are good quality and will last a long while, the t-shirts too. can't speak to how the dress shirts are. The cool hacker guys at my work wear jeans or simple trousers, t-shirts that fit well (not tight, but not like a size too big either), and blazers, but in corduroy or cotton, not a suitcoat type of blazer. There are cool ones at thrifts (how I wish women's had as many cool jackets) but make sure the shoulders fit and the sleeves are long enough, and then you can take it to a tailor and have it altered a little for a good fit.

Also what about getting some cool sneakers if you don't have them, I like my Pumas but Gola are cool I think, Asics, Adidas basic black (Samba, not the shell toe) always stylish. I really like APC, french label, if you go to the men's section they have some looks to check out - simple, classic, stylish. (OK maybe not the denim jumpsuit, but the other things.) They are relatively expensive but just to get an idea of what goes together..

Also don't throw out your punk rock tshirts.. :)
posted by citron at 8:34 PM on July 2, 2008 [1 favorite]

I don't really belong to any tribes,

Yes you do. It's the one who doesn't care about clothes.

One thing I do every so often is to pick up a GQ or Esquire and look in there for clothes I like. I look at who makes them and then look around online at the various different retailers and see what clothes they may offer.

Make it a habit to pick a couple things up a month.
posted by P.o.B. at 9:02 PM on July 2, 2008

It seems like you have a pretty casual workplace and personal style so I wouldn't worry about dressing up too much. Instead focus on below the belt. Many guys worry so much about what they look like at the eye level that they fail to think about what they look like below the waist so doing it right in the lower half is actually more noticeable.

Start with jeans. A good pair of well-fitting dark jeans in a price range higher than what you're used to. Don't be afraid to ask a female salesperson for help picking out styles and sizes - that's what they're there for. Pay attention to good fit at the waist, hips, and thighs and pay for them to get hemmed if the length is long. Get 2 or 3. It's going to hurt but this is a solid, long-term investment as good jeans last a long time.

Next, shoes. Like chrominance said, you can never go wrong with a pair of black Converse Chucks Taylors. Keep them clean with a toothbrush. And pick up another pair of sneakers with some color.

The trick for looking neat without too business/dressy is to have that one item that's casual. Button-down shirt with a punk jacket. Nice jacket/blazer with punk t-shirt. And make sure everything is fitted properly - snug but not tight.
posted by junesix at 9:08 PM on July 2, 2008

Best answer: Here's your little mantra: fit and material. You don't need to dress up -- you may want to, down the road, but for now stay casual because that is where you are -- but you do need to wear clothes that fit well, and that are made from good quality materials.

Fit starts with "not too tight, not too loose." Shirts, pay attention to shoulders and belly (and length if your torso is longer or shorter than average). Pants, pay attention to waist and butt, and make sure the inseam is a dignified length (neither dragging on the ground nor ready for the next flood).

Materials should generally be natural, with exceptions for hiking gear, safety apparel, and dress-up costumes like the guys in the photo you linked. Small percentages of stuff like lycra or whatever can add a nice touch to shirts and pants sometimes, but when in doubt default to 100% cotton/wool/linen/etc. Don't buy anything that doesn't feel good to the touch -- almost always, the better the material the better it feels when you stroke it, pinch it, and rub it between your fingers.

Unless you are getting a lot of compliments on your cords, a better day-to-day choice is probably jeans. Get a classic cut that actually fits -- the ultra ultra ultra tight look that some young guys wear doesn't work if you are in your 30s and carrying extra pounds. By the same token, the ultra-baggy look doesn't work for most guys, either. Get jeans that fit, and test for bending over / crawling around -- you don't need the plumber butt problem. If you want to look a bit less polished, work pants from companies like Carhartts tend to have a very flattering cut, at the expense of looking quite so white collar.

For shirts, t-shirts that fit are ok, but can be tricky if you have a belly. Better are guyaberas and other woven shirts made to be worn untucked (think Hawaiian shirts but without the painfully loud colors) that, again, actually fit. Loud funky 1970s patterns are fine, though watch the fit on those in case they are made to be tucked in or for guys without a belly.

Accessories really matter. Belt should be of a nice quality material; shoes should be ok-looking (can be Converse or hand-stitched Italian, as long as it is a deliberate choice that looks good with your other clothes); watches are one of the only pieces of jewelry most men wear so pick with care; try not to have too many cellphones/pagers/sliderules/toolkits hanging off of your belt, especially outside of work. Socks should fit (so they don't fall down all the time) and unless you are at the gym should not be white. (Similarly, no shorts unless you are the beach or the gym, either.)

Don't be afraid of color. Or rather, be deliberate and strategic about color. All black is ok, but hodgepodge isn't so great. If you have zero clue about color (which is fine, many people don't), take photos of different combinations of clothes and have a trusted friend (who does have a clue) lend a hand.
posted by Forktine at 9:35 PM on July 2, 2008 [2 favorites]

Best answer: "I don't rock jerseys, I'm 30-plus. I wear a crisp pair of jeans and a button-up"
- Jay-Z

McNulty: "They have a word for a guy who pays that much attention to his clothes."
Bunk: "Yeah, it's 'GROWNUP'."
- The Wire

I think its a hard transition to make, but your 30's is a really good time to start dressing like a grownup. That doesn't mean becoming lame and giving up all your punk-rock cred. It just means that it is far more appropriate to dress like a man than a boy. (I bet you've seen a woman in her 30's or 40's who dresses like a candy raver or hippie chick or goth girl? A style way too young for her that ends up making her look older than she is and clueless to boot? I think grown men dressing like teenagers is the same thing.)

So, to that end, some advice: (And apologies in advance if I'm assuming too much about your current wardrobe. If I'm off-base, just smile and say "I dress better than THAT, man!")

- Get clothes that fit you properly. Not too tight or too loose. Pants the right length. Tailors can do wonders adjusting things, and they don't charge much. If this is the only change you make, it will be a big one.
- Jeans should be dark, or naturally worn. (No washes or bleaches or treatments to your denim.) Blue not black.
- Try some pants. I like straight front (non-pleated) dockers. (Pleats tend to look dorky.) Heather gray slacks are a favorite of mine; they can dress up or dress down easily, go well with light or black shirts. Black pants make you look like a waiter, flat gray pants make you look like a janitor; its the texture that looks good.
- Avoid tons of stuff printed/embroidered on your clothes. Some band or funny t-shirts are ok, but look out for it on jackets, pants, etc; its a very young trendy look.
- Shirts with collars are good; shirts with collars and a straight bottom hem are great if you prefer to wear them untucked. (Guayabera shirts or camp shirts are good, bowling shirts if theyre not too cheesy.)
- Shoes, as opposed to sneakers. Women notice shoes, as do men who write performance appraisals and approve loans.) This doesn't mean you have to be uncomfortable at all. (The sneaker-styled shoes are actually worse looking than sneakers, though, most of the time.) Look for semi-classic comfortable shoes. I really like Clark's desert boots and Bjorn loafers for very hip and very comfortable grownup shoes. Rockport also makes some good-looking but very comfy shoes.
- Color isn't a bad thing just so long as you take it easy. It actually looks much better than all gray/all black/all neutral tones.
- Certain colors look good on you, others do not. (For me, for example; blues look great. Reds and greens tend to make my pale skin look ruddy or sallow, respectively.) Most women have learned this from childhood; ask a woman you know what would be good colors on you if you are having trouble figuring it out.
- Think about all the layers and the little details. The color & appearance of your undershirt collar showing at your neck, or your socks when they show. (Which they will.) Don't let the sleeves of a t-shirt droop down lower than the sleeves of a short-sleeve collared shirt. No white tube socks with slacks and shoes. Match your belt color to your shoe color. (Which only really need to be black or brown, maybe cordovan. You're too old for red or blue shoes, and way too young for white shoes.)

The very best advice I can give you is to try lots of things on. Honestly evaluate how it feels ON YOU; if it's not comfortable, forget it. Then look in the triple mirror; does it look good ON YOU? If not, forget it. (This sounds insultingly basic, but I have to remind myself of those two things all the time. I've wasted a ton of money in my life on clothes that I liked in theory but not in practice.)

The next best advice I can give is don't buy yourself a whole new wardrobe in one go. Buy a couple things from different places and wear them for a while. The ones you like and maybe get compliments on, buy a couple more. Maybe the same color, maybe slightly different color/style. Instead of one massive budget-breaking shopping trip eating up your whole Saturday, instead pick up a couple things once every 2 or three weeks.

And relax. Enjoy. Don't worry about the boxes and labels, that's kid stuff. The whole point of dressing well is to be comfortable and look your best, which contributes immensely to feeling your best.
posted by Cranialtorque at 11:00 PM on July 2, 2008

Not sure where you live, but the two best-answers you have marked above are what I would think of as good advice. As far as practicality and where to go - I am not sure where you are, geographically, but check out a Macy's or similar - we find great stuff for my husband on the sale racks there. Perry Ellis and Marc Ecko are good standbys. Some of the Marc Ecko stuff is weird, but there are edgy looking buttondowns that you can wear with nice jeans that don't look so "minivan." My husband is 36, for what it's worth, and he does not look ridiculous wearing these things. Look for stuff with details that make it interesting. If you have someone you know who has good fashion sense, or who will just be honest with you ("No, dude, yellow is a really bad idea.") then take them with you.
posted by Medieval Maven at 5:13 AM on July 3, 2008

Response by poster: Thanks to everyone for the advice—this has actually really helped me figure out what I'm trying to do.

I may have overstated the punk/hacker thing. I've never been punk, exactly (and I agree that it would be a silly thing to worry about at the age of 31)—and I'm not out to prove anything with my clothing—but the Middle America, polos-and-khakis, department-store look just skeezes me out. I mean, I love Fugazi, but when I say "punk rock", I just mean a general disgust with whitebread culture. As for the hacker thing: I at least know not to wear white Reeboks, clothes that don't fit, or shirts for open-source projects :)

I actually really like a lot of Calvin Klein stuff, and some of the Kenneth Cole Reaction line. I think maybe I just need some funkier stuff to complement that and offset its department-store-ness—vintage stuff, maybe some Marc Jacobs. Fear not; I'm keeping the more rugged/outdoorsy stuff, and the occasional shirt that says "OMG KILL GEORGE BUSH & FACE-FUCK JESUS WITH A CROWBAR".*

Thanks again!

* I do not actually own a shirt that says this.
posted by greenie2600 at 7:51 AM on July 3, 2008

Don't assume you'll find everything you want in one store. A nice shirt here, a nice pair of jeans there ...

Look online at some as it's often easier to pin down something you like, then view in the store. I've found reasonable success at H&M, The Gap, Banana Republic, Urban Outfitters, and surprisingly Benetton. However, I've found if I just walk into any of these store I can find feck all, maybe it's harder to parse everything in person! ;) And sometime I'll find SFA (Sweet F**K All) in all of them ... Also I've found that show "Queer Eye For The Straight Guy" quite helpful in stimulating me to try different clothes that what I'd normally wear.

Luck
posted by zaphod at 12:56 PM on July 3, 2008

I like the Ben Sherman recommendation, and I also think a sort of greaser look can work well for combining smart-dresser/counterculture/grown-up punk, as well as being pretty cute if one's not stick-thin.

Looking at photos, like others have said, is great for figuring out what you like, and you sound totally logic-minded enough to pick out patterns of "yeah, that!" once you've done it a bit. I like this guy's style on wardrobe remix, although you might hate it.

Also, colour totally doesn't need to be extrovert, and combining it right can be smooth sailing to style - a bit of reading into colour theory might help if you're not up on it already. Don't go too obvious or too bright, unless you're confident in it, but pale block colours with greys or other neutrals are awesome, and primaries with grey and black can be great. Beware of accidental Christmas Elf/nautical colour combinations.

Accessories (seriously), also - a good jacket topped off with a scarf or the right hat might work, or adding colour with something like an awesome (and terrifyingly pricey) freitag bag.

One thing I'm learning (and I'm a girl, but not fashiony and yet interested in aesthetics) is that like any other composition, a bit of messy is best offset by formality/tidyness/cleanness, so rocking a band t-shirt with fancy pants and a jacket is super (bizarrely, although maybe slightly by numbers, Hugh Laurie's wardrobe in House totally nails this).

Oh, and with the shoes, if you're out of your depth, get advice from someone. I have a soft spot for Camper sort of things, which you might not share, but going for "first job in supermarket junior management" shiny office shoes will fall flatter than skipping the shoe stage entirely.
posted by carbide at 12:57 PM on July 3, 2008 [1 favorite]

If you like Kenneth Cole, something I've found is that nothing in the Kenneth Cole shop fits me at all. I usually either wear a L or an XL, depending on the cut. (I'm a big guy, more gut than I should really have, but not obese thankyouverymuch.) At the Kenneth Cole shop, XL is uncomfortably small on me... like a medium in other places. However, if I go to Macy's, their Kenneth Cole shirts are completely normal sized. I think this goes for other designers too, I've noticed it with Ben Sherman as well. The shop is for model-thin dudes, but they do another line for average American physiques. Go figure.

Another thing I should mention is a watch. Aside from a wedding band, it's really the only piece of jewelry most men can pull off. Having a couple nice watches, for different states of dressiness, isn't a bad idea. Maybe a nice stainless-steel band one, maybe a nice leather-band one for dressier occasions. Less is more in terms of design. I like the Victorinox watches, Swatch makes some tasteful ones amidst all the novelties, Seiko has some nice designs too. Android has some very unique designs. Like this one I recently picked up. (It's actually really useful, as I live in NY and work with lots of folks in CA.)
posted by Cranialtorque at 5:03 PM on July 3, 2008

I think you're over thinking it. Dressing like prep doesn't make you a prep. Dressing like a banker doesn't make you one. Dressing like a emo doesn't make you one.

You know how much fun people have at costume parties? Well, that should be your approach. Every day I play a little game with myself whilst standing at the wardrobe; what costume will I wear today? The important thing is that clothes don't define who you are, but rather are like the frame of a painting.

Don't worry about clothes not feeling 'you', you just need to relax and enjoy it. The best dressed people are those that are comfortable in what they are wearing. So, wear things you wouldn't normally wear. As much as it should be an individual thing, draw on others for advice. I bet you'll have a few friends that are well known amongst your social circle for always looking well-dressed. Talk to them, go shopping with them, and try and pick up a few things.

I'm really fond of Ralph Lauren; their style is very classic and elegant. Stay away from the stuff that is too trendish. That's probably good advice until you get into your grove; just go for the basics. Simple things done well will always impress. Country Road, an Australian brand, is good at this approach of simple done well.

Try new outfits, take pictures and post them on this thread. We'll all be happy to tell you what works and what doesn't.
posted by oxford blue at 5:05 AM on July 4, 2008 [1 favorite]

Two suggestions:
1. Vintage and consignment stores. They reduce the feeling of being a department store tool (and they're environmental, bro!). I've found the stuff I bought in those places to last a long time. For the price of an average shirt, you can get really well-made stuff: consignment store stuff was originally really expensive, and in the past, clothes just tended to be made better.
2. Laundering and fabric care. I had a long story here but the short version is that I realized that buying nice clothes is only a quarter of the battle. The longer battle is to keep them nice-looking daily by ironing them (or pulling them out of the drier before the wrinkles set and hanging them up), and in the long run by laundering them in a way that doesn't prematurely age them.
posted by salvia at 11:08 AM on July 5, 2008

" ... the Middle America, polos-and-khakis, department-store look just skeezes me out ... "

I so agree with you there.
posted by zaphod at 6:44 PM on July 7, 2008